Compound and organic light-emitting device including the same

ABSTRACT

A compound is represented by Formula 1. An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the compound represented by Formula 1. The compound represented by Formula 1 suppresses or reduces the generation of dark spots by chelating metal that migrates from an electrode.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2019-0085206, filed on Jul. 15, 2019, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND 1. Field

One or more embodiments of the present disclosure relate to a compoundand an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices that,as compared with other devices in the art, have wide viewing angles,high contrast ratios, short response times, and excellentcharacteristics in terms of brightness, driving voltage, and responsespeed, and produce full-color images.

The organic light-emitting device may include a first electrode on asubstrate, and a hole transport region, an emission layer, an electrontransport region, and a second electrode, which are sequentially on thefirst electrode. Holes provided from the first electrode may move towardthe emission layer through the hole transport region, and electronsprovided from the second electrode may move toward the emission layerthrough the electron transport region. Carriers, such as holes andelectrons, recombine in the emission layer to produce excitons. Then,the excitons are transitioned (e.g., transition or relax) from anexcited state to a ground state, thereby generating light.

SUMMARY

One or more embodiments of the present disclosure include a holetransport compound having high efficiency characteristics, as comparedwith an existing compound, and serving to suppress or reduce thegeneration of dark spots by chelating a metal that migrates from anelectrode, and a device including the same.

Additional aspects of embodiments will be set forth in part in thedescription which follows and, in part, will be apparent from thedescription, or may be learned by practice of the presented embodiments.

An aspect of an embodiment of the present disclosure provides a compoundrepresented by Formula 1:

In Formula 1,

A may be a single bond linked X₃ with X₄, or A may be a fused C₄-C₆₀carbocyclic group or a fused C₁-C₆₀ heterocyclic group,

X₁ may be N, C, or C(R₁₁), X₂ may be N, C, or C(R₁₂), X₃ may be N, C, orC(R₁₃), X₄ may be N, C, or C(R₁₄), X₅ may be N, C, or C(R₁₅), and X₆ maybe N, C, or C(R₁₆),

Y₁ may be N or C(R₂₁), Y₂ may be N or C(R₂₂), Y₃ may be N or C(R₂₃), andat least one of Y₁ to Y₃ may be N,

R₁ to R₄, R₁₁ to R₁₆, and R₂₁ to R₂₃ may each independently be selectedfrom hydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

two neighboring substituents selected from R₁ to R₄, R₁₁ to R₁₆, and R₂₁to R₂₃ may be linked with each other to form a ring,

When A is a single bond linking X₃ with X₄, each of X₁, X₂, X₅, and X₆is CH, each of X₃ and X₄ is C, and R₁ may be excluded from beinghydrogen,

L may be selected from a substituted or unsubstituted C₄-C₆₀ carbocyclicgroup and a substituted or unsubstituted C₁-C₆₀ heterocyclic group,

When A is benzene, L or a moiety including Y₁ to Y₃ may be linked with acarbon of position 3 (numerals 2 and 3 are carbon positions where L; orthe moiety including Y₁ to Y₃ (m=0) is linked to the moiety includingA),

m may be an integer from 0 to 3,

a may be 1 or 2,

b may be an integer from 1 to 4,

c and d may each independently be an integer from 1 to 5,

At least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁—C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ arylenegroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀ heteroarylene group, the substituted monovalent non-aromaticcondensed polycyclic group, the substituted monovalent non-aromaticcondensed heteropolycyclic group, the substituted C₄-C₆₀ carbocyclicgroup, and the substituted C₁-C₆₀ heterocyclic group may be selectedfrom:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

Another aspect of an embodiment of the present disclosure provides anorganic light-emitting device including:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrodeand including an emission layer,

wherein the organic layer includes the compound represented by Formula1.

Another aspect of an embodiment of the present disclosure provides anelectronic apparatus including a thin-film transistor and the organiclight-emitting device, wherein the thin-film transistor includes asource electrode, a drain electrode, an activation layer, and a gateelectrode, and the first electrode of the organic light-emitting deviceis in electrical contact with one of the source electrode and the drainelectrode of the thin-film transistor.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects of embodiments will become apparent and morereadily appreciated from the following description of the embodiments,taken in conjunction with the accompanying drawings in which:

FIGS. 1 to 4 are schematic views of a structure of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the embodiments are merely described herein below, byreferring to the figures, to explain aspects of embodiments of thepresent description. As used herein, the term “and/or” includes any andall combinations of one or more of the associated listed items.Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list.

External quantum efficiency (next) used in a light-emitting materiallayer may be obtained (or calculated) utilizing the following equation.

η_(ext)=η_(int)×Γ×Φ×η_(out-coupling)

(wherein, η_(int): internal quantum efficiency, Γ: charge balancefactor, Φ: radiative quantum efficiency, η_(out-coupling): out couplingefficiency).

Charge balance factor (r) refers to a balance of a hole and an electronforming an exciton and generally has a value of “1” on the assumption of1:1 matching of 100%. Radiative quantum efficiency (Φ) is a valueinvolved in luminescence efficiency of an actual light-emitting materialand depends on fluorescence quantum efficiency of a dopant in ahost-dopant system.

Internal quantum efficiency (ηint) refers to a ratio at which agenerated exciton is converted into light that is emitted and has alimited value of up to 0.25 in the case of a fluorescent material. Whena hole and an electron are recombined to form an exciton, singletexcitons and triplet excitons are generated at a ratio of 1:3 accordingto arrangements of electron spin. However, only the singlet excitonsparticipate in light emission from the fluorescent material, and theremaining 75% of the triplet excitons do not participate in lightemission from the fluorescent material.

Out coupling efficiency (η_(out-coupling)) refers to a ratio of lightextracted to the outside from the emitted light. When isotropicmolecules are thermally deposited to form a thin film, individuallight-emitting molecules do not have a constant orientation (e.g., thesame orientation) and exist in a random orientation state (e.g., theindividual light-emitting molecules may be randomly oriented). Outcoupling efficiency in such a random orientation state is generallyassumed to be 0.2.

Therefore, in view of the above, maximum luminescence efficiency of anorganic light-emitting diode device using a fluorescent material as theonly light emitting material is about 5% or less. In order to overcomethe low efficiency of the fluorescent material, a phosphorescentmaterial has been developed which has a light-emitting mechanism thatconverts both singlet excitons and triplet excitons into light. In thecase of red light and green light, a phosphorescent material having highluminescence efficiency has been developed, but in the case of bluelight, a phosphorescent material having satisfactory luminescenceefficiency and reliability has not been developed. Therefore, thedevelopment of a fluorescent material having satisfactory reliabilityand being capable of increasing luminescence efficiency by increasingquantum efficiency is desired.

An aspect of an embodiment of the present disclosure provides a compoundrepresented by Formula 1:

In Formula 1,

A may be a single bond linking X₃ with X₄, or A may be a fused C₄-C₆₀carbocyclic group or a fused C₁-C₆₀ heterocyclic group,

X₁ may be N, C, or C(R₁₁), X₂ may be N, C, or C(R₁₂), X₃ may be N, C, orC(R₁₃), X₄ may be N, C, or C(R₁₄), X₅ may be N, C, or C(R₁₅), and X₆ maybe N, C, or C(R₁₆),

Y₁ may be N or C(R₂₁), Y₂ may be N or C(R₂₂), Y₃ may be N or C(R₂₃), andat least one selected from Y₁ to Y₃ may be N,

R₁ to R₄, R₁₁ to R₁₆, and R₂₁ to R₂₃ may each independently be selectedfrom hydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₂-C₆₀ alkenyl group, asubstituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

two neighboring substituents selected from R₁ to R₄, R₁₁ to R₁₆, and R₂₁to R₂₃ may be linked with each other to form a ring,

When A is a single bond linking X₃ with X₄, each of X₁, X₂, X₅, and X₆is CH, each of X₃ and X₄ is C, and R₁ may be excluded from beinghydrogen,

L may be selected from a substituted or unsubstituted C₄-C₆₀ carbocyclicgroup and a substituted or unsubstituted C₁-C₆₀ heterocyclic group,

When A is benzene, L or a moiety including Y₁ to Y₃ may be linked with acarbon of position 3 (numerals 2 and 3 are carbon positions where L; orthe moiety including Y₁ to Y₃ (m=0) is linked to the moiety includingA),

m may be an integer from 0 to 3,

a may be 1 or 2,

b may be an integer from 1 to 4,

c and d may each independently be an integer from 1 to 5,

at least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ arylenegroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀ heteroarylene group, the substituted monovalent non-aromaticcondensed polycyclic group, the substituted monovalent non-aromaticcondensed heteropolycyclic group, the substituted C₄-C₆₀ carbocyclicgroup, and the substituted C₁-C₆₀ heterocyclic group may be selectedfrom:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁) and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

For example, when A is benzene and b is 2 or more, neighboring R₂(s) maybe linked with each other to form a ring.

In the compound represented by Formula 1 according to one or moreembodiments, a stabilized form of a molecular structure has a flatmolecular structure without rotation (e.g., in the flat molecularstructure the pendant groups are not rotated out of the plane of themolecule). This molecular structure was confirmed based on a result ofgeometry optimization using density functional theory calculationsperformed utilizing Dmol3 software (available from Accelrys). The flatmolecular structure of embodiments of the present disclosure provides astrong oscillator strength, which causes the molecules of the compoundrepresented by Formula 1 to be aligned in the same (e.g., substantiallythe same) direction during deposition. The alignment of the molecules inthe same (e.g., substantially the same) direction facilitates hole andelectron movement, as compared with a random molecular structure (and/ora random orientation of the deposited material).

For example, as an example of the compound represented by Formula 1,when a compound having the following structure is geometry-optimized,

the following result may be obtained:

In some embodiments, the compound represented by Formula 1 includes twonitrogen atoms in

and thus, metal ion chelation by the compound represented by Formula 1may be facilitated. Therefore, the diffusion into an emission layer ismade impossible or unlikely by chelating metal ions migrating from anelectrode. The generation of dark spots from metal ions that migratefrom an electrode may be suppressed or reduced to prevent or reduce theoccurrence of defective pixels of a panel.

In one embodiment, in Formula 1 X₁ to X₆ may each be C(R₁₁), C(R₁₂),C(R₁₃), C(R₁₄), C(R₁₅), C(R₁₆).

In one embodiment, in Formula 1 X₂ and X₅ may each be C(R₁₂) and C(R₁₅),and X₁ and X₆ may each be N.

In one embodiment, in Formula 1 X₂ and X₅ may each be N, and X₁ and X₆may each be C(R₁₁) and C(R₁₆).

In one embodiment, A may be a single bond linking X₃ with X₄, acyclopentane, a benzene, a naphthalene or a quinoxaline.

In one embodiment, in Formula 1 R₂ to R₄ may each be hydrogen ordeuterium.

In one embodiment, in Formula 1 L may be a phenylene group, anaphthylene group, a phenanthrenylene group, an anthracenylene group, apyrenylene group, a chrysenylene group, a pyridinylene group, apyrazinylene group, a pyrimidinylene group, a pyridazinylene group, aquinolinylene group, an isoquinolinylene group, a quinoxalinylene group,a quinazolinylene group, a carbazolylene group, or a triazinylene group.When m is 2 or more, each L may be the same or different.

In one embodiment, Formula 1 may be one of the following Formula 1-1 to1-7:

In Formulae 1-1 to 1-4 and 1-7, R′₂ and R″₂ may each independently bethe same as defined in connection with R₂ in Formula 1. In Formula 1-5,R₁ may be excluded from being hydrogen. In Formulae 1-1 to 1-7, thesubstituents, subscripts, symbols, and the like may be the same asdescribed with respect to Formula 1.

In one embodiment, R₁ in Formula 1 may be selected from hydrogen,deuterium, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a phenanthrenyl group, an anthracenyl group, a pyrenylgroup, a chrysenyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, acarbazolyl group, a benzofuropyridyl group, a dibenzofuranyl group, adibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, anda phenanthrolinyl group.

In one embodiment, R₁ in Formula 1 may be hydrogen, deuterium, or agroup represented by one of Formulae 2a and 2b:

In Formulae 2a and 2b, R₂₁ to R₂₃ may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amino group, an amidino group, a hydrazinogroup, a hydrazono group, a carboxylic acid group or a salt thereof, asulfonic acid group or a salt thereof, a phosphoric acid group or a saltthereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, abiphenyl group, a terphenyl group, a naphthyl group, a phenanthrenylgroup, an anthracenyl group, a pyrenyl group, a chrysenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group,a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, anda phenanthrolinyl group, a21 may be an integer from 1 to 4, a22 may be 1or 2, a23 may be an integer from 1 to 3, and * indicates a binding siteto a neighboring atom. When a21, a22, and a23 are each 2 or more, two ormore R₂₁(s), two or more R₂₂(s), and two or more R₂₃(s) may be identicalto or different from each other.

In one embodiment, the compound represented by Formula 1 may be one ofthe following compounds:

The expression “(an organic layer) includes at least one compound,” asused herein, may include a case in which “(an organic layer) includesidentical compounds represented by Formula 1” and a case in which “(anorganic layer) includes two or more different compounds represented byFormula 1”.

For example, the organic layer may include, as the compound representedby Formula 1, only Compound 1-1. In this regard, Compound 1-1 may existonly in the emission layer of the organic light-emitting device. In oneor more embodiments, the organic layer may include, as the compound,Compound 1-1 and Compound 2-1. In this regard, Compound 1-1 and Compound2-1 may exist in an identical layer (for example, Compound 1 andCompound 2 may all exist in an emission layer), or different layers (forexample, Compound 1-1 may exist in an emission layer and Compound 2-1may exist in an electron transport layer).

Another aspect of an embodiment of the present disclosure provides anorganic light-emitting device including:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrodeand including an emission layer,

wherein the organic layer includes the compound represented by Formula1.

In one embodiment,

the first electrode of the organic light-emitting device may be ananode,

the second electrode of the organic light-emitting device may be acathode, and

the organic layer may further include a hole transport region betweenthe first electrode and the emission layer and an electron transportregion between the emission layer and the second electrode,

the hole transport region may include a hole injection layer, a holetransport layer, a buffer layer, an electron blocking layer, or anycombination thereof, and

the electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

In one embodiment, the emission layer may be a fluorescence emissionlayer.

In one embodiment, the compound represented by Formula 1 may be used inthe hole transport region. For example, the compound represented byFormula 1 may be used in the hole transport layer.

Another aspect of an embodiment of the present disclosure provides anelectronic apparatus including the organic light-emitting device and athin-film transistor, wherein the first electrode of the organiclight-emitting device may be in electrical contact with one of a sourceelectrode and a drain electrode of the thin-film transistor.

The term “an organic layer,” as used herein, refers to a single layerand/or a plurality of layers between the first electrode and the secondelectrode of an organic light-emitting device. A material included inthe “organic layer” is not limited to an organic material.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment. The organic light-emitting device10 includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of an organic light-emitting device accordingto an embodiment and a method of manufacturing an organic light-emittingdevice according to an embodiment will be described in connection withFIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally under the first electrode 110or above the second electrode 190. For use as the substrate, thesubstrate may be a glass substrate or a plastic substrate, each havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials having a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, a semi-reflectiveelectrode, or a transmissive electrode. When the first electrode 110 isa transmissive electrode, a material for forming a first electrode maybe selected from indium tin oxide (ITO), indium zinc oxide (IZO), tinoxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, butembodiments of the present disclosure are not limited thereto. In one ormore embodiments, when the first electrode 110 is a semi-transmissiveelectrode or a reflectable electrode, a material for forming a firstelectrode may be selected from magnesium (Mg), silver (Ag), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), and any combinations thereof, but embodimentsof the present disclosure are not limited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

Organic Layer 150

The organic layer 150 is on the first electrode 110. The organic layer150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer and an electrontransport region between the emission layer and the second electrode190.

Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, spiro-TPD, spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), PANI/DBSA (polyaniline/dodecylbenzenesulfonic acid),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA), andpolyaniline/poly(4-styrenesulfonate) (PANI/PSS):

A thickness of the hole transport region may be from about 100 Å toabout 10,000 Å, for example, about 100 Å to about 3,000 Å. When the holetransport region includes at least one selected from a hole injectionlayer and a hole transport layer, a thickness of the hole injectionlayer may be in a range of about 100 Å to about 9,000 Å, for example,about 100 Å to about 1,000 Å, and a thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, for exampleabout 100 Å to about 1,500 Å. When the thicknesses of the hole transportregion, the hole injection layer, and the hole transport layer arewithin these ranges, suitable or satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block or reduce the flow of electrons from anelectron transport region. The emission auxiliary layer and the electronblocking layer may include the materials as described herein above.

p-Dopant

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive (e.g., electrically conductive) properties. Thecharge-generation material may be homogeneously or non-homogeneouslydispersed in the hole transport region.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a lowest unoccupied molecularorbital (LUMO) energy level of −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In one embodiment, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least one ofR₂₂₁ to R₂₂₃ may have at least one substituent selected from a cyanogroup, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substituted with —F, aC₁-C₂₀ alkyl group substituted with —C₁, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

Emission Layer in Organic Layer 150

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, and a blue emission layer. Inone or more embodiments, the emission layer may have a stacked structureof two or more layers selected from a red emission layer, a greenemission layer, and a blue emission layer, in which the two or morelayers contact each other or are separated from each other. In one ormore embodiments, the emission layer may include two or more materialsselected from a red light-emitting material, a green light-emittingmaterial, and a blue light-emitting material, in which the two or morematerials are mixed with each other in a single layer to emit whitelight.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

In the emission layer, an amount of the dopant may be in a range ofabout 0.01 parts by weight to about 15 parts by weight based on 100parts by weight of the host, but embodiments of the present disclosureare not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellent emissioncharacteristics may be obtained without a substantial increase indriving voltage.

The emission layer may include a host.

Host in Emission Layer

In one or more embodiments, the host may further include a compoundrepresented by Formula 2 below:

In Formula 2,

Ar₁ and Ar₂ may each independently be selected from a substituted orunsubstituted C₆-C₆₀ aryl group and a substituted or unsubstitutedC₁-C₆₀ heteroaryl group,

R₁ to R₇ may each independently be selected from hydrogen, deuterium, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromaticcondensed polycyclic group, and a substituted or unsubstitutedmonovalent non-aromatic condensed heteropolycyclic group,

at least one substituent selected from the substituted C₁-C₆₀ alkylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The host may include at least one of the following compounds, butembodiments of the present disclosure are not limited thereto:

Phosphorescent Dopant Included in Emission Layer in Organic Layer 150

The phosphorescent dopant may include an organometallic complexrepresented by Formulae 401 or 402 below:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1 is 2 or more, two or more L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein, when xc2 is two or more, two or more L₄₀₂(s) may be identicalto or different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be selected from a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)—*′,*—C(Q₄₁₁)(Q₄₁₂)—*′, *—C(Q₄₁₁)═C(Q₄₁₂)—*, *—C(Q₄₁₁)=*′, or *═C(Q₄₁₁)=*′,wherein Q₄₁₁ and Q₄₁₂ may each independently be hydrogen, deuterium, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃),—N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and—P(═O)(Q₄₀₁)(Q₄₀₂), wherein Q₄₀₁ to Q₄₀₃ may each independently beselected from a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ arylgroup, and a C₁-C₂₀ heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one embodiment, A₄₀₁ and A₄₀₂ in Formula 402 may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) X₄₀₁ and X₄₀₂ may each be nitrogen at thesame time.

In one or more embodiments, R₄₀₁ and R₄₀₂ in Formula 402 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantanyl group, a norbornanylgroup, and anorbornenylgroup;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁) and —P(═O)(Q₄₀₁)(Q₄₀₂),

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, when xc1 in Formula 401 is 2 or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, whichis a linking group, or two A₄₀₂(s) in two or more L₄₀₁(s) may optionallybe linked via X₄₀₈, which is a linking group (see Compounds PD1 to PD4and PD7). X₄₀₇ and X₄₀₈ may each independently be a single bond, *—O—*′,*—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)—*′, *—C(Q₄₁₃)(Q₄₁₄)—*′, or*—C(Q₄₁₃)═C(Q₄₁₄)—*′(wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but embodiments of the present disclosure are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from halogen, diketone (forexample, acetylacetonate), carboxylic acid (for example, picolinate),—C(═O), isonitrile, —CN, and phosphorus (for example, phosphine, orphosphite), but embodiments of the present disclosure are not limitedthereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

Fluorescent Dopant in Emission Layer

The fluorescent dopant may include an arylamine compound or astyrylamine compound.

The fluorescent dopant may include a compound represented by Formula 501below:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₄-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer from 1 to 6.

In one embodiment, in Formula 501, Ar₅₀₁ may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD22:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto:

Quantum Dot in Emission Layer

In one embodiment, the emission layer included in the organiclight-emitting device may include a quantum dot material.

The quantum dot is a particle having a crystal structure having a sizeof several to tens of nanometers and may include hundreds to thousandsof atoms.

Because the quantum dot is very small in size, the quantum dot mayexhibit a quantum confinement effect. The quantum confinement effectrefers to a phenomenon in which a band gap of an object increases whenthe object becomes smaller than a nanometer size. Therefore, when lightof a wavelength having an energy greater than the band gap of thequantum dot is irradiated onto the quantum dot, the quantum dot absorbsthe light and is promoted to an excited state, and emits light of a setor specific wavelength when it returns to a ground state. At this time,the wavelength of the emitted light has a value corresponding to theband gap.

A core of the quantum dot may include a group II-VI compound, a groupIII-VI compound, a group III-V compound, a group IV-VI compound, a groupIV compound, a group I—III-VI compound, or any mixture thereof.

The group IV-VI compound may be selected from: a binary compoundselected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and any mixture thereof;a ternary compound selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe,PbSTe, SnPbS, SnPbSe, SnPbTe, and any mixture thereof; and a quaternarycompound selected from SnPbSSe, SnPbSeTe, SnPbSTe, and any mixturethereof. The group IV element may be selected from Si, Ge, and anymixture thereof. The group IV compound may be a binary compound selectedfrom SiC, SiGe, and any mixture thereof.

The binary compound, the ternary compound, or the quaternary compoundmay exist in particles at uniform (e.g., substantially uniform)concentration, or may exist in the same particle in a state in which aconcentration distribution is partially different. In addition, thebinary compound, the ternary compound, or the quaternary compound mayhave a core-shell structure in which one quantum dot surrounds anotherquantum dot. An interface between the core and the shell may have aconcentration gradient in which the concentration of certain atomsexisting in the shell decreases along a direction toward the center.

In one or more embodiments, the quantum dot may have a core-shellstructure including a core with the above-described nanoparticles and ashell surrounding the core. The shell of the quantum dot may serve as aprotective layer for maintaining semiconductor characteristics bypreventing or reducing chemical degeneration of the core and/or mayserve as a charging layer for imparting electrophoretic characteristicsto the quantum dot. The shell may be a single layer or a multilayer. Aninterface between the core and the shell may have a concentrationgradient in which the concentration of certain atoms existing in theshell decreases along a direction toward the center. Examples of theshell of the quantum dot may include a metal or non-metal oxide, asemiconductor compound, or any combination thereof.

For example, examples of the metal or non-metal oxide may include abinary compound such as SiO₂, Al₂O₃, TiO₂, ZnO, MnO, Mn₂O₃, Mn₃O₄, CuO,FeO, Fe₂O₃, Fe₃O₄, CoO, Co₃O₄, NiO, or a ternary compound such asMgAl₂O₄, CoFe₂O₄, NiFe₂O₄, or CoMn₂O₄, but embodiments of the presentdisclosure are not limited thereto.

In addition, examples of the semiconductor compound may include CdS,CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe,HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and the like, butembodiments of the present disclosure are not limited thereto.

A full width of half maximum (FWHM) of an emission wavelength spectrumof the quantum dot may be about 45 nm or less, for example, about 40 nmor less, for example, about 30 nm or less. When the FWHM of the emissionwavelength spectrum of the quantum dot is within this range, colorpurity or color reproduction may be improved. In addition, light emittedthrough such quantum dot is irradiated in omnidirection (e.g.,substantially every direction), thereby improving a wide viewing angle.

In addition, the quantum dot is a quantum dot generally used in the art,and is not particularly limited. For example, a spherical, pyramidal,multi-arm, or cubic nanoparticle, nanotube, nanowire, nanofiber, ornanoplate particle may be used.

The quantum dot may adjust the color of emitted light according to theparticle size. Therefore, the quantum dot may be configured to emitvarious suitable emission colors such as blue, red, or green.

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from ahole blocking layer, an electron control layer, an electron transportlayer, and an electron injection layer, but embodiments of the presentdisclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or an electron transport layer/electron injection layerstructure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region may include the organic layer includingthe compound represented by Formula 1.

The electron transport region may further include, in addition to thecompound represented by Formula 1, for example, a compound representedby Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe11)-R₆₀₁]_(xe21).  Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₄-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₁(s) in the number of xe21 may include the π electron-depletednitrogen-containing ring.

In one embodiment, Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, a compound represented by Formula 601 may berepresented by Formula 601-1 below:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be defined the same as xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, R₆₀₁ and R₆₁₁ to R₆₁₃ in Formula 601 and601-1 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ may be the same as described herein above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one selected from 2,9-dimethyl-4,7-diphenyl-1, 10-phenanthroline(BCP), 4,7-diphenyl-1, 10-phenanthroline (Bphen), Alq3, BAlq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

In one embodiment, the electron transport region may include a phosphineoxide-containing compound (for example, TSPO1 used in the followingexamples or the like), but embodiments of the present disclosure are notlimited thereto. In one embodiment, the phosphine oxide-containingcompound may be used in a hole blocking layer in the electron transportregion, but embodiments of the present disclosure are not limitedthereto.

Thicknesses of the buffer layer, the hole blocking layer, and theelectron control layer may each be in a range of about 20 Å to about1,000 Å, for example, about 30 Å to about 300 Å. When the thicknesses ofthe buffer layer, the hole blocking layer, and the electron controllayer are within these ranges, the electron blocking layer may haveexcellent electron blocking characteristics or electron controlcharacteristics without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed herein above, the electron transport layer may have suitableor satisfactory electron transport characteristics without a substantialincrease in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described herein above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy phenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190. Theelectron injection layer may directly contact the second electrode 190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compoundmay be selected from LiF, Li₂, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), orBa_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, Sc₂O₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described herein above, and aligand coordinated with a metal ion of the alkali metal complex, thealkaline earth-metal complex, or the rare earth metal complex may beselected from hydroxy quinoline, hydroxy isoquinoline, hydroxybenzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxyphenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole,hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxyphenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine,phenanthroline, and cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

The electron injection layer may include (or consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkali metalcompound, an alkaline earth-metal compound, a rare earth metal compound,an alkali metal complex, an alkaline earth-metal complex, a rare earthmetal complex, or any combinations thereof, as described herein above.In one or more embodiments, the electron injection layer may furtherinclude an organic material. When the electron injection layer furtherincludes an organic material, an alkali metal, an alkaline earth metal,a rare earth metal, an alkali metal compound, an alkaline earth-metalcompound, a rare earth metal compound, an alkali metal complex, analkaline earth-metal complex, a rare earth metal complex, or anycombinations thereof may be homogeneously or non-homogeneously dispersedin a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedherein above, the electron injection layer may have suitable orsatisfactory electron injection characteristics without a substantialincrease in driving voltage.

Second Electrode 190

The second electrode 190 may be on the organic layer 150 having such astructure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Description of FIGS. 2 to 4

FIG. 2 is a schematic view of an organic light-emitting device 20according to an embodiment. The organic light-emitting device 20includes a first capping layer 210, the first electrode 110, the organiclayer 150, and the second electrode 190, which are sequentially stackedin this stated order. FIG. 3 is a schematic view of an organiclight-emitting device 30 according to an embodiment. The organiclight-emitting device 30 includes the first electrode 110, the organiclayer 150, the second electrode 190, and a second capping layer 220,which are sequentially stacked in this stated order. FIG. 4 is aschematic view of an organic light-emitting device 40 according to anembodiment. The organic light-emitting device 40 includes the firstcapping layer 210, the first electrode 110, the organic layer 150, thesecond electrode 190, and the second capping layer 220, which aresequentially stacked in this stated order.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110 and the first capping layer 210 toward the outside,wherein the first electrode 110 may be a semi-transmissive electrode ora transmissive electrode. In the organic layer 150 of each of theorganic light-emitting devices 30 and 40, light generated in an emissionlayer may pass through the second electrode 190 and the second cappinglayer 220 toward the outside, wherein the second electrode 190 may be asemi-transmissive electrode or a transmissive electrode.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescence efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial. The organic capping layer may include polyethyleneterephthalate, polyethylene naphthalate, polycarbonate, polyimide,polyethylene sulfonate, polyoxymethylene, polyarylate,hexamethyldisiloxane, acryl-based resin (e.g., polymethylmethacrylate,polyacrylic acid, etc.), or any combination thereof.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include at least one materialselected from carbocyclic compounds, heterocyclic compounds, amine-basedcompounds, porphyrine derivatives, phthalocyanine derivatives, anaphthalocyanine derivatives, alkali metal complexes, and alkalineearth-based complexes. The carbocyclic compound, the heterocycliccompound, and the amine-based compound may be optionally substitutedwith a substituent containing at least one element selected from O, N,S, Se, Si, F, Cl, Br, and I.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include anamine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto:

Hereinbefore, the organic light-emitting device according to anembodiment has been described in connection with FIGS. 1 to 4, butembodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to 200° C. by taking into account a material to be includedin a layer to be formed, and the structure of a layer to be formed.

Apparatus

The organic light-emitting device may be included in various suitableapparatuses. For example, a light-emitting apparatus, an authenticationapparatus, or an electronic apparatus, which includes the organiclight-emitting device, may be provided.

The light-emitting apparatus may further include, in addition to theorganic light-emitting device, a thin film transistor including a sourceelectrode and a drain electrode. One of the source electrode and thedrain electrode of the thin film transistor may be in electrical contactwith one of the first electrode and the second electrode of the organiclight-emitting device. The light-emitting apparatus may be used asvarious suitable displays, light sources, and/or the like.

The authentication apparatus may be, for example, a biometricauthentication apparatus for authenticating an individual by usingbiometric information of a biometric body (for example, a fingertip, apupil, and/or the like).

The authentication apparatus may further include, in addition to theorganic light-emitting device, a biometric information collector.

The electronic apparatus may be applied to personal computers (forexample, a mobile personal computer), mobile phones, digital cameras,electronic organizers, electronic dictionaries, electronic gamemachines, medical instruments (for example, electronic thermometers,sphygmomanometers, blood glucose meters, pulse measurement devices,pulse wave measurement devices, electrocardiogram (ECG) displays,ultrasonic diagnostic devices, and/or endoscope displays), fish finders,various suitable measuring instruments, meters (for example, meters fora vehicle, an aircraft, and a vessel), projectors, and/or the like, butembodiments of the present disclosure are not limited thereto.

General Definition of at Least Some of the Substituents

The term “C₁-C₆₀ alkyl group,” as used herein, refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group,” as used herein, refers to a hydrocarbongroup having at least one carbon-carbon double bond at a main chain(e.g., in the middle) or at a terminal end (e.g., the terminus) of theC₂-C₆₀ alkyl group, and examples thereof include an ethenyl group, apropenyl group, and a butenyl group. The term “C₂-C₆₀ alkenylene group,”as used herein, refers to a divalent group having substantially the samestructure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group,” as used herein, refers to a hydrocarbongroup having at least one carbon-carbon triple bond at a main chain(e.g., in the middle) or at a terminal end (e.g., the terminus) of theC₂-C₆₀ alkyl group, and examples thereof include an ethynyl group, and apropynyl group. The term “C₂-C₆₀ alkynylene group,” as used herein,refers to a divalent group having substantially the same structure asthe C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group,” as used herein, refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group,” as used herein, refers to amonovalent saturated hydrocarbon monocyclic group having 3 to 10 carbonatoms, and examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group,” as used herein, refers to adivalent group having substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group,” as used herein, refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group,” as used herein, refers to a divalentgroup having substantially the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity(e.g., is not aromatic), and examples thereof include a cyclopentenylgroup, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group,” as used herein, refers to a divalent grouphaving substantially the same structure as the C₃-C₁₀ cycloalkenylgroup.

The term “C₁-C₁₀ heterocycloalkenyl group,” as used herein, refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup,” as used herein, refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group,” as used herein, refers to a monovalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms,and the term “C₆-C₆₀ arylene group,” as used herein, refers to adivalent group having a carbocyclic aromatic system having 6 to 60carbon atoms. Non-limiting examples of the C₆-C₆₀ aryl group include aphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenylgroup, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ arylgroup and the C₆-C₆₀ arylene group each include two or more rings, therings may be fused to each other (e.g., combined together).

The term “C₁-C₆₀ heteroaryl group,” as used herein, refers to amonovalent group having a carbocyclic aromatic system that has at leastone heteroatom selected from N, O, Si, P, and S as a ring-forming atom,in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylenegroup,” as used herein, refers to a divalent group having a carbocyclicaromatic system that has at least one heteroatom selected from N, O, Si,P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be condensed with each other(e.g., combined together).

The term “C₆-C₆₀ aryloxy group,” as used herein, refers to —OA₁₀₂(wherein A₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthiogroup,” as used herein, indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀aryl group).

The term “monovalent non-aromatic condensed polycyclic group,” as usedherein, refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other (e.g.,combined together), only carbon atoms as ring-forming atoms, and noaromaticity in its entire molecular structure (e.g., is not aromatic).An example of the monovalent non-aromatic condensed polycyclic group isa fluorenyl group. The term “divalent non-aromatic condensed polycyclicgroup,” as used herein, refers to a divalent group having substantiallythe same structure as the monovalent non-aromatic condensed polycyclicgroup.

The term “monovalent non-aromatic condensed heteropolycyclic group,” asused herein, refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other (e.g.,combined together), at least one heteroatom selected from N, O, Si, P,and S, other than carbon atoms, as a ring-forming atom, and noaromaticity in its entire molecular structure (e.g., is not aromatic).An example of the monovalent non-aromatic condensed heteropolycyclicgroup is a carbazolyl group. The term “divalent non-aromatic condensedheteropolycyclic group,” as used herein, refers to a divalent grouphaving substantially the same structure as the monovalent non-aromaticcondensed heteropolycyclic group.

The term “C₄-C₆₀ carbocyclic group,” as used herein, refers to amonocyclic or polycyclic group having 4 to 60 carbon atoms in which aring-forming atom is a carbon atom only. The term “C₄-C₆₀ carbocyclicgroup,” as used herein, refers to an aromatic carbocyclic group or anon-aromatic carbocyclic group. The C₄-C₆₀ carbocyclic group may be aring, such as benzene, a monovalent group, such as a phenyl group, or adivalent group, such as a phenylene group. In one or more embodiments,depending on the number of substituents connected to the C₄-C₆₀carbocyclic group, the C₄-C₆₀ carbocyclic group may be a trivalent groupor a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group,” as used herein, refers to a grouphaving substantially the same structure as the C₄-C₆₀ carbocyclic group,except that as a ring-forming atom, at least one heteroatom selectedfrom N, O, Si, P, and S is used in addition to carbon (the number ofcarbon atoms may be in a range of 1 to 60).

In the present specification, at least one substituent of thesubstituted C₄-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀ cycloalkylene group, thesubstituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkylgroup substituted with at least one selected from deuterium, —F, and acyano group, a C₆-C₆₀ aryl group substituted with at least one selectedfrom deuterium, —F, and a cyano group, a biphenyl group, and aterphenylgroup.

The term “Ph,” as used herein, refers to a phenyl group, the term “Me,”as used herein, refers to a methyl group, the term “Et,” as used herein,refers to an ethyl group, the term “ter-Bu” or “Bu^(t),” as used herein,refers to a tert-butyl group, and the term “OMe,” as used herein, refersto a methoxy group.

The term “biphenyl group,” as used herein, refers to “a phenyl groupsubstituted with a phenyl group”. In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′, as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The wording “Bwas used instead of A” used in describing Synthesis Examples refers tothat an identical molar equivalent of B was used in place of A.

EXAMPLES Synthesis Example: Synthesis of Compound Synthesis of Compound1-4

4,9-dibromoquinolino[7,8-h]quinoline (3.9 g, 10 mmol),2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-s-triazine (5.0 g, 11mmol), K₂CO₃ (2.8 g, 20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) wereadded to a schlenk tube, dried in a vacuum state for 2 hours, and thendissolved in tetrahydrofuran (THF) (100 mL). N₂-purged anhydrous EtOH(20 mL) was added thereto and stirred at a temperature of 80° C. for 24hours in a nitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of dichloromethane (DCM) anddistilled water, and an organic layer was separated therefrom. Theseparated organic layer was dried by using MgSO₄ and purified by columnchromatography (DCM/hexane (1:1, v/v)) to obtain Intermediate 1-4-A (3.1g, 5.0 mmol, yield: 50%).

Intermediate 1-4-A (6.2 g, 10 mmol), phenylboronic acid (1.5 g, 12mmol), K₂CO₃ (1.4 g, 10 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) wereadded to a schlenk tube, dried in a vacuum state for 2 hours, and thendissolved in dimethylformamide (DMF) (100 mL). N₂-purged anhydrous EtOH(20 mL) was added thereto and stirred at a temperature of 100° C. for 24hours in a nitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of DCM and distilled water,and an organic layer was separated therefrom. The separated organiclayer was dried by using MgSO₄ and purified by column chromatography(DCM) to obtain Compound 1-4 (4.8 g, 7.8 mmol, yield: 78%).

Synthesis of Compound-2-3

3.8-dibromo-1,10-phenanthroline (3.4 g, 10 mmol),2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-s-triazine (5.0 g, 11mmol), K₂CO₃ (2.8 g, 20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) wereadded to a schlenk tube, dried in a vacuum state for 2 hours, and thendissolved in DMF (100 mL). N₂-purged anhydrous EtOH (20 mL) was addedthereto and stirred at a temperature of 100° C. for 24 hours in anitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of DCM and distilled water,and an organic layer was separated therefrom. The separated organiclayer was dried by using MgSO₄ and purified by column chromatography(DCM/hexane (10:1, v/v)) to obtain Intermediate 2-3-A (4.4 g, 7.7 mmol,yield: 77%).

Intermediate 2-3-A (5.7 g, 10 mmol), phenylboronic acid (1.5 g, 12mmol), K₂CO₃ (1.4 g, 10 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) wereadded to a schlenk tube, dried in a vacuum state for 2 hours, and thendissolved in THF (100 mL). N₂-purged anhydrous EtOH (20 mL) was addedthereto and stirred at a temperature of 80° C. for 24 hours in anitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of chloroform and distilledwater, and an organic layer was separated therefrom. The separatedorganic layer was dried by using MgSO₄ and purified by columnchromatography (chloroform) to obtain Compound 2-3 (4.1 g, 7.3 mmol,yield: 73%).

Synthesis of Compound 2-7

Intermediate 2-3-A (5.7 g, 10 mmol) was dissolved in anhydrous toluene(50 mL)/THF (10 mL) in a nitrogen atmosphere, and n-BuLi (5 mL, 1.2equiv. 2.5 M in hexane) was slowly added thereto at a temperature of−78° C. The reaction mixture was stirred at a temperature of −78° C. for1 hour, and trimethylborate (1.2 mmol) was added thereto. HCl (12 mL, 2Msolution) was added thereto, and the solution was heated to roomtemperature. A separated organic layer was washed by using distilledwater and brine solution. The solution was dried by using MgSO₄, and asolvent was removed therefrom under reduced pressure. A product obtainedtherefrom was washed several times by using hot n-hexane to obtainIntermediate 2-7-A (3.7 g, 6.9 mmol, yield: 69%).

Intermediate 2-7-A (5.3 g, 10 mmol),6-bromo-4-phenylbenzofuro[3,2-b]pyridine (3.2 g, 10 mmol), K₂CO₃ (2.8 g,20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) were added to a schlenktube, dried in a vacuum state for 2 hours, and then dissolved in1,4-dioxane (100 mL). N₂-purged anhydrous MeOH (20 mL) was added theretoand stirred at a temperature of 130° C. for 48 hours in a nitrogenatmosphere. The reaction mixture was cooled to room temperature, and asolvent was removed therefrom under reduced pressure. The resultant waswashed by using an excess of chloroform and distilled water, and anorganic layer was separated therefrom. The separated organic layer wasdried by using MgSO₄ and purified by column chromatography (chloroform)to obtain Compound 2-7 (2.9 g, 4.0 mmol, yield: 40%).

Synthesis of Compound 2-5

1,4-dibromonaphthalene (2.9 g, 10 mmol),2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-s-triazine(5.0 g, 11 mmol), K₂CO₃ (2.8 g, 20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35mmol) were added to a schlenk tube, dried in a vacuum state for 2 hours,and then dissolved in DMF (100 mL). N₂-purged anhydrous EtOH (20 mL) wasadded thereto and stirred at a temperature of 100° C. for 24 hours in anitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of DCM and distilled water,and an organic layer was separated therefrom. The separated organiclayer was dried by using MgSO₄ and purified by column chromatography(DCM/hexane (2:1, v/v)) to obtain Intermediate 2-5-A (3.5 g, 6.8 mmolyield: 68%).

Intermediate 2-5-A (5.1 g, 10 mmol),(8-cyano-1,10-phenanthrolin-3-yl)boronic acid (2.7 g, 11 mmol), K₂CO₃(2.8 g, 20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) were added to aschlenk tube, dried in a vacuum state for 2 hours, and then dissolved inDMF (100 mL). N₂-purged anhydrous EtOH (20 mL) was added thereto andstirred at a temperature of 100° C. for 48 hours in a nitrogenatmosphere. The reaction mixture was cooled to room temperature, and asolvent was removed therefrom under reduced pressure. The resultant waswashed by using an excess of chloroform and distilled water, and anorganic layer was separated therefrom. The separated organic layer wasdried by using MgSO₄ and purified by column chromatography (chloroform)to obtain Compound 2-5 (4.1 g, 6.4 mmol, yield: 64%).

Synthesis of Compound 6-1

5,5′-dibromo-2,2′-bipyrimidine (3.2 g, 10 mmol), phenylboronic acid (1.5g, 12 mmol), K₂CO₃ (1.4 g, 10 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol)were added to a schlenk tube, dried in a vacuum state for 2 hours, andthen dissolved in THF (100 mL). N₂-purged anhydrous EtOH (20 mL) wasadded thereto and stirred at a temperature of 80° C. for 24 hours in anitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of DCM and distilled water,and an organic layer was separated therefrom. The separated organiclayer was dried by using MgSO₄ and purified by column chromatography(dichloromethane) to obtain Intermediate 6-1-A (2.4 g, 7.7 mmol, yield:77%).

Intermediate 6-1-A (3.1 g, 10 mmol),2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-s-triazine (5.0 g, 11 mmol), K₂CO₃ (2.8 g,20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35 mmol) were added to a schlenktube, dried in a vacuum state for 2 hours, and then dissolved in1,4-dioxane (100 mL). N₂-purged anhydrous EtOH (20 mL) was added theretoand stirred at a temperature of 120° C. for 24 hours in a nitrogenatmosphere. The reaction mixture was cooled to room temperature, and asolvent was removed therefrom under reduced pressure. The resultant waswashed by using an excess of chloroform and distilled water, and anorganic layer was separated therefrom. The separated organic layer wasdried by using MgSO₄ and purified by column chromatography(chloroform/hexane (5:1, v/v)) to obtain Compound 6-1 (2.9 g, 5.4 mmol,yield: 54%).

Synthesis of Compound 7-10

2,7-dibromodipyrazino[2,3-f:2′,3′-h]quinoxaline (3.9 g, 10 mmol),phenylboronic acid (1.5 g, 12 mmol), K₂CO₃ (2.8 g, 20 mmol), andPd(PPh₃)₄ (0.41 g, 0.35 mmol) were added to a schlenk tube, dried in avacuum state for 2 hours, and then dissolved in DMF (100 mL). N₂-purgedanhydrous EtOH (20 mL) was added thereto and stirred at a temperature of100° C. for 24 hours in a nitrogen atmosphere. The reaction mixture wascooled to room temperature, and a solvent was removed therefrom underreduced pressure. The resultant was washed by using an excess of DCM anddistilled water, and an organic layer was separated therefrom. Theseparated organic layer was dried by using MgSO₄ and purified by columnchromatography (DCM) to obtain Intermediate 7-10-A (1.8 g, 4.6 mmol,yield: 46%).

Intermediate 7-10-A (3.9 g, 10 mmol),2,4-diphenyl-6-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-s-triazine(5.0 g, 11 mmol), K₂CO₃ (2.8 g, 20 mmol), and Pd(PPh₃)₄ (0.41 g, 0.35mmol) were added to a schlenk tube, dried in a vacuum state for 2 hours,and then dissolved in 1,4-dioxane (100 mL). N₂-purged anhydrous EtOH (20mL) was added thereto and stirred at a temperature of 120° C. for 48hours in a nitrogen atmosphere. The reaction mixture was cooled to roomtemperature, and a solvent was removed therefrom under reduced pressure.The resultant was washed by using an excess of DCM and distilled water,and an organic layer was separated therefrom. The separated organiclayer was dried by using MgSO₄ and purified by column chromatography(DCM) to obtain Compound 7-10 (3.5 g, 5.7 mmol, yield: 57%).

¹H NMR of each of Compounds synthesized according to Synthesis Examplesis shown in Table 1.

Synthesis methods of compounds other than Compounds shown in Table 1 mayalso be easily recognized by those of ordinary skill in the art uponreferring to the synthesis mechanisms and source materials describedherein above.

TABLE 1 Compound ¹H NMR (DMSO-d₆, 500 MHz) 1-4 7.15(d, 2H), 7.25(d, 2H),7.41-7.50(m,9H), 7.79-7.82(dd, 4H), 7.96(d, 2H), 8.12(d, 2H), 8.36(d,4H), 8.87 (d, 2H) 2-3 7.25(d, 2H), 7.46-7.50(m,11H), 7.91- 7.96(m, 3H),8.12(d, 1H), 8.20(s, 2H), 8.40(d, 4H) 2-5 7.24(d, 2H), 7.46-7.52(m,8H),7.84- 7.96(m, 4H), 8.06-8.12(dd, 2H), 8.20(s, 1H), 8.26 (s, 1H), 8.36(d, 4H), 8.81(s, 1H), 8.95-9.02(dd, 2H), 9.40 (s, 1H) 2-7 7.25(d, 2H),7.41-7.51(m, 12H), 7.80 (d, 1H), 7.91-8.02(m, 5H), 8.12(d, 1H)), 8.19(s,1H), 8.26 (s, 1H), 8.36 (d, 4H), 8.61(s, 1H) 6-1 7.20(d, 2H),7.46-7.51(m, 11H), 7.96 (d, 2H), 8.32 (d, 4H), 9.61(s, 4H) 7-107.49-7.59(m, 9H), 7.94-8.00 (dd, 6H), 8.23 (s, 1H), 8.26 (d, 2H), 8.75(s, 4H), 8.86 (d, 2H)

Simulation Evaluation

HOMO, LUMO, triplet energy level, singlet energy level, diploe, andoscillator strength (OSC) of Compounds 1-1 to 8-1 according to one ormore embodiments, TPBi, and Compounds 101, 102, 103, and 104 wereobtained a simulation (name: Gaussian, version: B3LYP/6-31 G*; e.g., thesimulation included density functional theory calculations performedutilizing a B3LYP hybrid functional and a 6-31 G* basis set conductedutilizing the Gaussian software package) and compared, and resultsthereof are shown in Table 2.

TABLE 2 Com- HOMO LUMO Eg Triplet Singlet pound (eV) (eV) (eV) (eV) (eV)dipole OSC 1-1 −5.76 −2.13 3.63 2.45 2.85 2.34 f = 0.0002 1-2 −5.76−2.03 3.73 2.46 2.99 2.26 f = 0.0175 1-3 −5.87 −2.15 3.72 2.46 2.99 4.11f = 0.0090 1-4 −5.77 −2.02 3.75 2.46 2.99 2.19 f = 0.0228 2-1 −5.81−2.06 3.74 2.47 3.15 4.69 f = 0.3850 2-2 −5.71 −1.94 3.77 2.49 3.16 3.03f = 0.4203 2-3 −6.02 −2.09 3.93 2.60 3.23 3.08 f = 1.1958 2-4 −6.14−2.21 3.92 2.62 3.22 4.67 f = 0.8183 2-5 −6.15 −2.48 3.67 2.51 3.23 7.02f = 0.5377 2-6 −6.06 −2.24 3.81 2.60 3.10 3.46 f = 0.7561 2-7 −5.98−2.12 3.87 2.60 3.11 3.01 f = 0.9681 3-1 −5.89 −2.08 3.82 2.62 3.24 3.27f = 1.0522 3-2 −6.00 −2.19 3.80 2.64 3.23 4.88 f = 0.8623 4-1 −6.16−2.51 3.65 2.40 2.91 0.60 f = 1.3958 4-2 −6.34 −2.61 3.73 2.48 2.91 2.58f = 1.0225 5-1 −5.98 −2.07 3.91 2.67 3.53 2.93 f = 1.5003 5-2 −6.12−2.19 3.94 2.74 3.24 4.65 f = 0.7465 6-1 −6.18 −2.27 3.91 2.65 3.13 0.04f = 0.0872 6-2 −6.30 −2.40 3.90 2.69 3.10 2.03 f = 0.0646 7-1 −5.68−1.80 3.88 2.44 3.03 0.74 f = 0.0003 7-2 −5.71 −1.67 4.04 2.50 3.29 3.20f = 0.6133 7-3 −5.91 −1.80 4.11 2.69 3.27 3.93 f = 0.9819 7-4 −6.02−2.40 3.62 2.49 2.97 1.97 f = 0.0113 7-5 −5.97 −1.79 4.18 2.76 3.28 3.62f = 1.3198 7-6 −6.04 −2.11 3.93 2.75 3.19 1.86 f = 0.0020 7-7 −5.66−1.86 3.80 2.41 3.01 1.74 f = 0.0310 7-8 −5.67 −1.79 3.87 2.44 3.28 4.56f = 0.7059 7-9 −6.00 −1.93 4.07 2.63 3.24 1.85 f = 1.0795 7-10 −6.14−2.42 3.72 2.48 2.92 1.48 f = 1.1623 7-11 −5.97 −1.93 4.04 2.72 3.331.73 f = 1.3297 7-12 −6.15 −2.19 3.96 2.67 3.13 1.90 f = 0.0849 8-1−6.08 −2.30 3.78 2.63 3.40 4.15 f = 1.4309 TPBi −5.89 −1.51 4.38 2.793.74 1.04 f = 0.0031 100 −5.90 −2.27 3.62 2.17 3.19 0.72 f = 0.0379 101−6.33 −2.30 4.03 2.72 3.64 0.06 f = 0.0139 102 −6.25 −2.30 3.95 2.723.42 1.26 f = 0.0002 103 −5.79 −2.23 3.57 2.28 3.12 1.19 f = 0.0494

(in Table 2, “Eg” indicates a gap between HOMO and LUMO.)

From Table 2, it can be seen that Compounds 1-1 to 8-1 according to oneor more embodiments have stronger oscillator strength than TPBi andCompounds 100, 101, 102, and 103. For the dipole value, it can be seenthat Compounds 1-1 to 8-1 according to one or more embodiments are morepolar than TPBi and Compounds 100, 101, 102, and 103. Therefore, thedipole moments of Compounds 1-1 to 8-1 according to one or moreembodiments are expected to be located in the plane forming themolecules. This may be expected to have a more constant (e.g., moreuniform) orientation than TPBi and Compounds 100, 102, and 103 in themolecular arrangement during deposition.

Manufacture of Organic Light-Emitting Device Comparative Example 1

As an anode, a Corning 15 Ω/cm² (1,200 Å) ITO glass substrate was cut toa size of 50 mm×50 mm×0.5 mm, sonicated with isopropyl alcohol and purewater each for 5 minutes, and then cleaned by exposure to ultravioletrays and ozone for 30 minutes. Then, the ITO glass substrate wasprovided to a vacuum deposition apparatus.

An existing material (HAT-CN) was vacuum-deposited on the ITO glasssubstrate to form a hole injection layer having a thickness of 100 Å,and a hole transport compound TAPC was vacuum-deposited on the holeinjection layer to form a hole transport layer having a thickness of 300Å.

mCP and TPBe were co-deposited on the hole transport layer at a weightratio of 94:6 wt % to form an emission layer having a thickness of 300Å.

T2T was deposited on the emission layer to form a hole blocking layerhaving a thickness of 100 Å, TPBi was deposited on the hole blockinglayer to form an electron transport layer having a thickness of 550 Å.

LiF was deposited on the electron transport layer to form an electroninjection layer having a thickness of 8 Å, and Al was deposited on theelectron injection layer to form an electrode having a thickness of1,000 Å.

Comparative Example 2

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 100 wasused instead of TPBi in forming an electron transport layer.

Comparative Example 3

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 101 wasused instead of TPBi in forming an electron transport layer.

Comparative Example 4

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 102 wasused instead of TPBi in forming an electron transport layer.

Comparative Example 5

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 103 wasused instead of TPBi in forming an electron transport layer.

Example 1

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 1-4 wasused instead of TPBi in forming an electron transport layer.

Example 2

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 2-3 wasused instead of TPBi in forming an electron transport layer.

Example 3

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 2-7 wasused instead of TPBi in forming an electron transport layer.

Example 4

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 6-1 wasused instead of TPBi in forming an electron transport layer.

Example 5

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 7-10 wasused instead of TPBi in forming an electron transport layer.

Example 6

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 2-3 wasused instead of TPBi in forming an electron transport layer, andCompound 200-3 was used instead of mCP as a host.

Example 7

An organic light-emitting device was manufactured in substantially thesame manner as in Comparative Example 1, except that Compound 2-5 wasused instead of TPBi in forming an electron transport layer, andCompound 200-5 was used instead of mCP as a host.

The driving voltage, luminance, external quantum efficiency (EQE), andlifespan of the organic light-emitting devices manufactured according toExamples 1 to 7 and Comparative Examples 1 to 5 were manufactured, andresults thereof are shown in Table 3.

TABLE 3 Electron transporting Driving Lifespan material Host voltage (V)EQE(%) T95 (hr) Comparative TPBi mCP 4.8 3.6 1 Example 1 Comparative 100mCP 4.2 5.0 11 Example 2 Comparative 101 mCP 4.3 3.4 18 Example 3Comparative 102 mCP 4.8 3.9 5 Example 4 Comparative 103 mCP 3.7 6.7 24Example 5 Example 1 1-4 mCP 3.8 6.1 25 Example 2 2-3 mCP 3.3 9.4 51Example 3 2-7 mCP 3.5 8.3 43 Example 4 6-1 mCP 3.9 5.6 13 Example 5 7-10 mCP 3.9 4.3 10 Example 6 2-3 200-3 3.2 10.2 87 Example 7 2-5 200-53.4 9.9 71

From Table 3, it can be seen that the organic light-emitting devices ofExamples 1 to 7 exhibit excellent results, as compared with the organiclight-emitting devices of Comparative Examples 1 to 5. This isconsistent with that expected in the simulation results of Table 2.

The organic light-emitting device including the compound represented byFormula 1 may exhibit excellent efficiency and improved lifespan.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould be considered as available for other similar features or aspectsin other embodiments.

While one or more embodiments have been described with reference to thefigures, it will be understood by those of ordinary skill in the artthat various changes in form and details may be made therein withoutdeparting from the spirit and scope of the present disclosure as definedby the following claims, and equivalents thereof.

What is claimed is:
 1. A compound represented by Formula 1:

wherein, in Formula 1, A is a single bond linking X₃ with X₄, or A is afused C₄-C₆₀ carbocyclic group or a fused C₁-C₆₀ heterocyclic group, X₁is N, C, or C(R₁₁), X₂ is N, C, or C(R₁₂), X₃ is N, C, or C(R₁₃), X₄ isN, C, or C(R₁₄), X₅ is N, C, or C(R₁₅), and X₆ is N, C, or C(R₁₆), Y₁ isN or C(R₂₁), Y₂ is N or C(R₂₂), Y₃ is N or C(R₂₃), and at least one ofY₁ to Y₃ is N, R₁ to R₄, R₁₁ to R₁₆, and R₂₁ to R₂₃ are eachindependently selected from hydrogen, deuterium, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), two neighboring substituents selectedfrom R₁ to R₄, R₁₁ to R₁₆, and R₂₁ to R₂₃ are linked with each other toform a ring, when A is a single bond linking X₃ with X₄, each of X₁, X₂,X₅, and X₆ is CH, each of X₃ and X₄ is C, and R₁ is excluded from beinghydrogen, L is selected from a substituted or unsubstituted C₄-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀ heterocyclicgroup, when A is benzene, L or a moiety comprising Y₁ to Y₃ is linkedwith a carbon of position 3 (numerals 2 and 3 are carbon positions whereL; or the moiety comprising Y₁ to Y₃ is linked to the moiety includingA), m is an integer from 0 to 3, a is 1 or 2, b is an integer from 1 to4, c and d are each independently an integer from 1 to 5, at least onesubstituent of the substituted C₁-C₆₀ alkyl group, the substitutedC₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, thesubstituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ arylenegroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedC₁-C₆₀ heteroarylene group, the substituted monovalent non-aromaticcondensed polycyclic group, the substituted monovalent non-aromaticcondensed heteropolycyclic group, the substituted C₄-C₆₀ carbocyclicgroup, and the substituted C₁-C₆₀ heterocyclic group is selected from:deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group; a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, aC₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂),—B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, and a monovalentnon-aromatic condensed heteropolycyclic group; a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ toQ₂₃, and Q₃₁ to Q₃₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.
 2. Thecompound of claim 1, wherein X₁ is C or C(R₁₁), X₂ is C or C(R₁₂), X₃ isC or C(R₁₃), X₄ is C or C(R₁₄), X₅ is C or C(R₁₅), and X₆ is C orC(R₁₆).
 3. The compound of claim 1, wherein X₂ is C or C(R₁₂), X₅ is Cor C(R₁₅), and each of X₁ and X₆ is N.
 4. The compound of claim 1,wherein each of X₂ and X₅ is N, X₁ is C or C(R₁₁), and X₆ is C orC(R₁₆).
 5. The compound of claim 1, wherein A is a single bond linkingX₃ with X₄, or indicates a fused cyclopentane, a fused benzene, a fusednaphthalene, or a fused quinoxaline.
 6. The compound of claim 1, whereineach of R₂ to R₄ is hydrogen or deuterium.
 7. The compound of claim 1,wherein L is selected from a phenylene group, a naphthylene group, aphenanthrenylene group, an anthracenylene group, a pyrenylene group, achrysenylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a pyridazinylene group, a quinolinylene group, anisoquinolinylene group, a quinoxalinylene group, a quinazolinylenegroup, a carbazolylene group, and a triazinylene group.
 8. The compoundof claim 1, wherein Formula 1 is represented by one of Formulae 1-1 to1-7:

wherein, in Formulae 1-1 to 1-4 and 1-7, R′₂ and R″₂ are eachindependently the same as defined in connection with R₂ in Formula 1,and in Formula 1-5, R₁ is excluded from being hydrogen.
 9. The compoundof claim 1, wherein R₁ is selected from hydrogen, deuterium, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, aphenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, abenzofuropyridyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a triazinyl group, a benzimidazolyl group, and a phenanthrolinylgroup.
 10. The compound of claim 1, wherein R₁ is represented byhydrogen, deuterium, or a group represented by one of Formulae 2a and2b:

wherein, in Formulae 2a and 2b, R₂₁ to R₂₃ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amino group, an amidino group, ahydrazino group, a hydrazono group, a carboxylic acid group or a saltthereof, a sulfonic acid group or a salt thereof, a phosphoric acidgroup or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, aphenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, abenzimidazolyl group, and a phenanthrolinyl group, a21 is an integerfrom 1 to 4, a22 is 1 or 2, a23 is an integer from 1 to 3, and indicatesa binding site to a neighboring atom.
 11. The compound of claim 1,wherein the compound represented by Formula 1 is one of the followingcompounds:


12. An organic light-emitting device comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode and comprising anemission layer, wherein the organic layer comprises the compound ofclaim
 1. 13. The organic light-emitting device of claim 12, wherein thefirst electrode is an anode, the second electrode is a cathode, theorganic layer between the first electrode and the second electrode andcomprising the emission layer further comprises i) a hole transportregion between the first electrode and the emission layer and comprisinga hole injection layer, a hole transport layer, a buffer layer, anelectron blocking layer, or any combination thereof and ii) an electrontransport region between the emission layer and the second electrode andcomprising a hole blocking layer, an electron transport layer, anelectron injection layer, or any combination thereof.
 14. The organiclight-emitting device of claim 13, wherein the electron transport regioncomprises the compound represented by Formula
 1. 15. The organiclight-emitting device of claim 13, wherein the electron transport layercomprises the compound represented by Formula
 1. 16. The organiclight-emitting device of claim 13, wherein the compound chelates a metalcompound migrating from the cathode.
 17. The organic light-emittingdevice of claim 12, wherein, the emission layer comprises a host, andthe host comprises a compound represented by Formula 2:

wherein, in Formula 2, Ar₁ and Ar₂ are each independently selected froma substituted or unsubstituted C₆-C₆₀ aryl group and a substituted orunsubstituted C₁-C₆₀ heteroaryl group, R₁ to R₇ are each independentlyselected from hydrogen, deuterium, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, and asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, at least one substituent of the substitutedC₁-C₆₀ alkyl group, the substituted C₆-C₆₀ aryl group, the substitutedC₁-C₆₀ heteroaryl group, the substituted monovalent non-aromaticcondensed polycyclic group, and the substituted monovalent non-aromaticcondensed heteropolycyclic group is selected from: deuterium (-D), —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group;a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group; a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, and a monovalent non-aromaticcondensed heteropolycyclic group, each substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, aC₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ toQ₂₃, and Q₃₁ to Q₃₃ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromaticcondensed polycyclic group, a monovalent non-aromatic condensedheteropolycyclic group, a biphenyl group, and a terphenyl group.
 18. Theorganic light-emitting device of claim 17, wherein the compoundrepresented by Formula 2 is selected from the following compounds:


19. The organic light-emitting device of claim 12, wherein the emissionlayer comprises quantum dots.
 20. An electronic apparatus comprising: athin-film transistor; and the organic light-emitting device of claim 12,wherein the thin-film transistor comprises a source electrode, a drainelectrode, an activation layer, and a gate electrode, and the firstelectrode of the organic light-emitting device is in electrical contactwith one of the source electrode and the drain electrode of thethin-film transistor.